Your Retirement Milestones
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Early
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Healthcare
Medicare is federal health insurance for people 65 and older. Understanding when and how to enroll — and which supplemental coverage to add — can save you thousands per year.
Initial Enrollment Period (IEP)
March 2026 – September 2026(you turn 65: June 2026)
Enroll in the first 3 months for coverage to begin when you turn 65. Waiting until months 4–7 may delay your start date.
Your 7-month IEP opens 3 months before your 65th birthday. Missing it means waiting for the General Enrollment Period (Jan–Mar) with coverage starting July 1.
Still on employer coverage? A Special Enrollment Period (8 months after it ends) applies — no late penalty.
Already receiving Social Security at 65? You're auto-enrolled in Parts A and B.
HSA users: Medicare enrollment terminates HSA contributions — see the important HSA note below.
Original Medicare (A + B) covers 80% of approved costs. The remaining 20% — plus deductibles — is where supplemental insurance matters. Medigap Plans G and N cover the Part A deductible completely.
Part B: +10% per year missed. Permanent.
Part D: +1% per month without creditable drug coverage. Permanent.
Employer/union/TRICARE/VA coverage counts as creditable coverage — enroll within 63 days of losing it to avoid penalties.
• Online at ssa.gov/medicare
• Call 1-800-MEDICARE (1-800-633-4227)
• Local Social Security office
Your HSA is one of the best pre-retirement tools available. HSA funds grow tax-free, and withdrawals for qualified medical expenses are never taxed. After age 65, you can withdraw for any reason (taxed as ordinary income, like a traditional IRA) — but medical withdrawals remain completely tax-free. Building your HSA balance and deferring withdrawals until retirement maximizes this triple tax advantage.
The Medicare catch: It seems like a no-brainer to sign up for Medicare Part A at 65 — it's premium-free and covers hospital expenses your private insurance may not. But enrolling in any part of Medicare, including Part A, permanently terminates your ability to contribute to an HSA. You must also stop HSA contributions 6 months before your Medicare start date, because Part A can be retroactive up to 6 months.
Watch out for employer assumptions: Many employers with high-deductible health plans (HDHPs) will automatically stop your HSA contributions once you turn 65, assuming you'll enroll in Medicare. If you want to delay Medicare and keep contributing, you may need to proactively contact your HR department — but remember to stop contributions at least 6 months before you actually enroll.
Your Decision at 65
Every employer's medical plans are different. High-deductible plans are lower cost for companies, but they come with the benefit of HSAs — and some employers contribute to your HSA to help offset deductible costs. As you approach 65, you need to decide between two paths:
Path 1 — Delay Medicare, keep building your HSA
Don't sign up for any part of Medicare. Stay on your employer's HDHP and continue making HSA contributions. This preserves the triple tax advantage and lets your HSA balance keep growing. You'll need to make sure your employer doesn't auto-stop your HSA contributions at 65 — talk to HR. When you eventually retire or enroll in Medicare, stop HSA contributions at least 6 months beforehand.
Path 2 — Sign up for Part A (HSA contributions end)
Enroll in Part A for premium-free hospital coverage. This ends your HSA contributions, but your existing HSA balance can still be spent tax-free on qualified medical expenses and Medicare premiums. Now you need to decide how to cover non-hospital costs:
- Sign up for Part B + supplemental insurance: Drop your employer plan and let Medicare become your primary coverage. Compare the total cost of Part B premiums + Medigap or Medicare Advantage to what you're paying for your employer plan.
- Skip Part B, stay on employer insurance: Keep using your employer plan for doctor visits and outpatient care. However, without HSA contributions the high-deductible plan loses much of its attractiveness — consider switching to a non-HDHP option during your employer's open enrollment if available. When you eventually leave the employer plan, you'll have an 8-month Special Enrollment Period to sign up for Part B with no late penalty.
There is no one-size-fits-all answer. Review your employer's specific plan offerings, HSA employer match, premium costs, and your expected medical expenses before deciding.
Supplemental Coverage: Medigap vs. Medicare Advantage
Original Medicare leaves significant gaps. Most retirees choose one of two paths to fill them.
Private insurance that works alongside Original Medicare to cover its cost-sharing gaps. Plans are standardized by federal law (Plan A, B, C, D, F, G, K, L, M, N) — the same letter plan has identical benefits regardless of insurer.
Advantages
✓ Use any doctor or hospital that accepts Medicare nationwide
✓ No referrals needed for specialists
✓ Predictable, low out-of-pocket costs (especially Plan G)
✓ Most plans include foreign travel emergency coverage (80%)
Disadvantages
✗ Higher monthly premiums than Advantage
✗ No prescription drug coverage — need a separate Part D plan
✗ Medical underwriting applies outside Open Enrollment (can be denied or charged more based on health)
Best for: People who want maximum flexibility, travel, or have ongoing healthcare needs.
An all-in-one alternative to Original Medicare offered by private insurers. Includes Parts A and B coverage, usually Part D, and often dental, vision, and hearing.
Advantages
✓ Often $0 monthly premium
✓ May include dental, vision, hearing, fitness benefits
✓ Prescription drugs bundled (MAPD plans)
✓ Annual out-of-pocket cap (≤$9,250 in-network, 2026)
Disadvantages
✗ Network restrictions — HMO/PPO with in-network requirements
✗ Prior authorization often required for procedures
✗ Coverage limited when traveling — out-of-network costs can be high
✗ Plans change annually — benefits, networks, and costs may shift
Best for: People who want low premiums, are generally healthy, and stay in a defined geographic area.
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